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Indexed by:期刊论文

Date of Publication:2007-12-10

Journal:CARBOHYDRATE RESEARCH

Included Journals:SCIE、EI、PubMed、Scopus

Volume:342

Issue:17

Page Number:2657-2663

ISSN No.:0008-6215

Key Words:sucrose; esterification; regioselective; stannylene acetal

Abstract:Regioselective formation of 6-O-acylsucroses and 6,3'-di-O-acylsucroses in one pot with good yields was achieved for the first time by a typical acylation method of sucrose via its dibutylstannylene acetal. Pure monoesters at OH-6 and diesters at OH-6,3' obtained by these procedures were readily isolated by simple column chromatography, thus overcoming the main difficulties associated with regioselectivity, efficiency, and isolation techniques for the practical preparation. Explanations for the regioselectivities observed during this stannylene acetal-mediated reaction were also proposed based on the structures of the stannylene acetal in solution and the intramolecular migration of stannylenes. (c) 2007 Elsevier Ltd. All rights reserved.